149716-72-3

Basic information

• Product Name: (1R,2R,3S,5R)-Pinanediol Pyrrolidine-2R-boronate Hydrochloride
• Synonyms: (1R,2R,3S,5R)-Pinanediol Pyrrolidine-2R-boronate Hydrochloride;(2R)-2-[(3aR,4R,6R,7aS)-hexahydro-3a,5,5-triMethyl-4,6-Methano-1,3,2-benzodioxaborol-2-yl]pyrrolidine Hhydrochloride;[3aR-[2(R*),3aα,4β,6β,7aα]]-;(2S)-2-Pyrrolidineboronic acid (1S,2S,3R, 5S)-(+)-2,3-pinanediol ester hydrochloride;(2S)-2-[(3aR,4R,6R,7aS)-3a,5,5-Trimethylhexahydro-4,6-methano-1,2-benzoxaborol-2(3H)-yl]pyrrolidine hydrochloride;(2S)-2-Pyrrolidineboronic acid (1S,2S,3R
• CAS NO: 149716-72-3
• Molecular Formula: C14H27BClNO3
• Molecular Weight: 303.63308
• Product Categories: Boron Derivatives;Chiral Reagents;Heterocycles;Intermediates
• Mol File: 149716-72-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol
• CAS DataBase Reference: (1R,2R,3S,5R)-Pinanediol Pyrrolidine-2R-boronate Hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,3S,5R)-Pinanediol Pyrrolidine-2R-boronate Hydrochloride(149716-72-3)
• EPA Substance Registry System: (1R,2R,3S,5R)-Pinanediol Pyrrolidine-2R-boronate Hydrochloride(149716-72-3)

Safety Data

• Hazardous Substances Data: 149716-72-3(Hazardous Substances Data)

Usage

Uses

(1R,2R,3S,5R)-Pinanediol Pyrrolidine-2R-boronate Hydrochloride is used in the preparation of prolineboronate esters.

Upstream product

• 230299-05-5 bis-(+)-pinanediolato diboron 
• 1536530-89-8 C₁₈H₃₂BNO₃S 
• 1536530-69-4 C₁₈H₃₃BClNO₃S 
• 7647-01-0 hydrogenchloride 
• 205116-75-2 (1S,2S,3R,5S)-pinane-2,3-diyl (N-(1,1-dimethylethoxycarbonyl)pyrrolidin-2-yl)boronate 
• 18680-27-8 pinanediol 

Relevant articles and documents

A practical synthesis of L-valyl-pyrrolidine-(2R)-boronic acid: Efficient recycling of the costly chiral auxiliary (+)-pinanediol

A practical synthesis of L-valyl-pyrrolidine-(2R)-boronic acid (1) is detailed. A previously disclosed synthesis of 1 (Snow, R.; Kelly, T. R.; Adams, J.; Coutts, S.; Perry, C. (Boehringer Ingelheim Pharmaceuticals, Inc.). WO 93/10127, 1993) was significantly improved by developing an efficient process for recycling the costly chiral auxiliary (+)- pinanediol.

Proline boric acid compound and preparation method and applications thereof

The invention provides a compound whose structure is shown as a formula (I) or a salt thereof. The compound is a proline boric acid proteasome inhibitor compound, and has good proteasome inhibitory activity and excellent druggability. The structural formula of the compound is shown as the formula (I).

Asymmetric synthesis of stable α-aminoboronic esters catalyzed by N-heterocylic carbene and copper(i) chloride

Bis(pinanediolato)diboron (B2pnd2) was used as the nucleophile instead of bis(pinacolato)diboron in the stereospecific synthesis of α-aminoboronic esters catalysed by a triazole-based N-hetereocyclic carbene (NHC) and Cu(i) chloride.